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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 279865Generated: October 30, 2026

Methanol → Dimethyl 2,5-dimethyl-4-[2-(2-trimethylsilylethenyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

https://huagongshe.com/reaction/279865

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantMethyl acetoacetateHCID 7757—
ReactantMethyl 3-aminocrotonateHCID 643918—
Reactant2-(2-Trimethylsilylethenyl)benzaldehydeHCID 54301200—
ProductDimethyl 2,5-dimethyl-4-[2-(2-trimethylsilylethenyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylateHCID 74031287—

Reaction Steps

To the Compound 1a (3.1 mmol) in anhydrous methanol (8 ml) was added methyl 3-aminocrotonate (3.1 mmol) and methyl acetoacetate (3.1 mmol) and the resulting solution heated at reflux under nitrogen for 5 days. The solvent was removed in vacuo to yield a yellow oil which was purified by flash chromatography on silica gel eluted with hexane:diethyl ether (1:1) to afford Compound 1b as yellowish powder (Rf =0.3, m.p. 148°-150° C.).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04587253
Source datasetuspto-grants-1986_05
ORD IDord-96e60ece598b4b6fa5ed4d7b8e3d9461
Source noteuspto-grants-1986_05